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    City: Chestertown, MD
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    17 Properties Available In Chestertown

    17 Properties Available In Chestertown

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    MD >Chestertown >
    Market Insights
    106 QUEEN ST S, Chestertown, MD 21620
    1/92
    Open Sat 10AM-12PM

    $829,000

    3 Beds4 Baths2,472 SqFt

    106 QUEEN ST S, Chestertown, MD 21620

    MLS# MDKE2006152

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    517 ROUND TOP RD, Chestertown, MD 21620
    1/28
    Price Dropped by $25K

    $299,900

    3 Beds1 Bath1,248 SqFt

    517 ROUND TOP RD, Chestertown, MD 21620

    MLS# MDQA2017680

    Listed by Keller Williams Flagship

    Bright MLS (BMLS)
    104 CONLEY DR, Chestertown, MD 21620
    1/27
    Price Dropped by $7K

    $239,900

    3 Beds2 Baths1,280 SqFt

    104 CONLEY DR, Chestertown, MD 21620

    MLS# MDKE2006686

    Listed by Cummings & Co. Realtors

    Bright MLS (BMLS)
    104 ACORN DR, Chestertown, MD 21620
    1/26
    Price Dropped by $9K

    $275,000

    3 Beds3 Baths1,900 SqFt

    104 ACORN DR, Chestertown, MD 21620

    MLS# MDKE2006668

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    234 N COLLEGE AVE, Chestertown, MD 21620
    1/3
    Price Dropped by $10K

    $90,000

    2 Beds1 Bath1,296 SqFt

    234 N COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2006670

    Listed by Cummings & Co Realtors

    Bright MLS (BMLS)
    110 PROSPECT ST, Chestertown, MD 21620
    1/6
    Price Dropped by $5K

    $74,900

    3 Beds2 Baths2,210 SqFt

    110 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006626

    Listed by ANR Realty, LLC

    Bright MLS (BMLS)
    522 HIGH ST, Chestertown, MD 21620
    1/15
    Price Dropped by $49K

    $350,000

    2 Beds3 Baths1,518 SqFt

    522 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006614

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    240 MERGANSER DR, Chestertown, MD 21620
    1/55
    Price Dropped by $24K
    3D

    $365,000

    3 Beds2 Baths1,120 SqFt

    240 MERGANSER DR, Chestertown, MD 21620

    MLS# MDQA2016900

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    101 COLEMAN DR, Chestertown, MD 21620
    1/56
    Price Dropped by $5K

    $519,900

    3 Beds3 Baths2,268 SqFt

    101 COLEMAN DR, Chestertown, MD 21620

    MLS# MDQA2016624

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    139 PROSPECT ST, Chestertown, MD 21620
    1/28
    Under Contract

    $198,000

    3 Beds1 Bath1,200 SqFt

    139 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006250

    Listed by Redfin Corp

    Bright MLS (BMLS)
    8886 GEORGETOWN RD, Chestertown, MD 21620
    1/3
    Price Dropped by $5K

    $80,000

    4.03 Acres

    8886 GEORGETOWN RD, Chestertown, MD 21620

    MLS# MDKE2006634

    Listed by Samson Properties

    Bright MLS (BMLS)
    SANDY BOTTOM RD, Chestertown, MD 21620
    1/6
    Price Dropped by $20K

    $59,000

    1.95 Acres

    SANDY BOTTOM RD, Chestertown, MD 21620

    MLS# MDKE2006554

    Listed by Village Real Estate Company LLC

    Bright MLS (BMLS)
    104 MAPLE AVE #6, Chestertown, MD 21620
    1/27
    Active

    $1,920

    2 Beds2 Baths900 SqFt

    104 MAPLE AVE #6, Chestertown, MD 21620

    MLS# MDKE2006408

    Listed by Real Broker, LLC - Annapolis

    Bright MLS (BMLS)
    104 MAPLE AVE, Chestertown, MD 21620
    1/30
    Price Dropped by $119K

    $1,350,000

    10,540 Sqft Lot

    104 MAPLE AVE, Chestertown, MD 21620

    MLS# MDKE2006386

    Listed by Real Broker, LLC - Annapolis

    Bright MLS (BMLS)
    201 N LYNCHBURG ST, Chestertown, MD 21620
    1/13
    Price Dropped by $45K

    $750,000

    4,342 Sqft Lot

    201 N LYNCHBURG ST, Chestertown, MD 21620

    MLS# MDKE2006082

    Listed by RE/MAX Associates-Hockessin

    Bright MLS (BMLS)
    JOHNSONTOWN RD, Chestertown, MD 21620
    1/16
    Price Dropped by $10K

    $25,000

    0.9 Acres

    JOHNSONTOWN RD, Chestertown, MD 21620

    MLS# MDKE2005550

    Listed by Berkshire Hathaway HomeServices PenFed Realty

    Bright MLS (BMLS)
    515 WASHINGTON AVE, Chestertown, MD 21620
    1/4
    Price Dropped by $104K

    $795,000

    0.97 Acres Lot

    515 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2000776

    Listed by EShore

    Bright MLS (BMLS)
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    Bayside Realty
    Dale Hunter Jr
    +1(443) 829-5828
    dalehunterjr@baysiderealtymd.com
    23458 Scotts Ln, St Michaels, MD 21663, USA
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        Market Snapshot
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

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    Bayside Realty
    Dale Hunter Jr
    +1(443) 829-5828
    dalehunterjr@baysiderealtymd.com
    23458 Scotts Ln, St Michaels, MD 21663, USA
        Home
        Buy
        1. All Listings
        2. Featured Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Rent
        1. Rental Listings
        Featured Areas
        1. Easton Overview
        2. Denton Overview
        3. Trappe Overview
        4. Chestertown Overview
        5. Saint Michaels Overview
        6. Ridgely Overview
        7. Berlin Overview
        About
        1. My Team
        2. About Us
        3. Contact Us
        4. Reviews
        Market Snapshot
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility